14245-62-6

Basic information

• Product Name: Ethanesulfonic acid isopropyl ester
• Synonyms: Ethanesulfonic acid isopropyl ester;Isopropyl ethanesulfonate
• CAS NO: 14245-62-6
• Molecular Formula: C₅H₁₂O₃S
• Molecular Weight: 152.21198
• Mol File: 14245-62-6.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 237℃
• Flash Point: 97℃
• Appearance: /
• Density: 1.096
• Vapor Pressure: 0.0714mmHg at 25°C
• Refractive Index: 1.428
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: Ethanesulfonic acid isopropyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanesulfonic acid isopropyl ester(14245-62-6)
• EPA Substance Registry System: Ethanesulfonic acid isopropyl ester(14245-62-6)

Safety Data

• Hazardous Substances Data: 14245-62-6(Hazardous Substances Data)

Usage

Description

Ethanesulfonic acid isopropyl ester, also known as Propan-2-yl Ethane-1-sulfonate, is an organic compound with the chemical formula C6H14O3S. It is a colorless liquid with a slight odor and is soluble in water. This ester is known for its ability to inhibit certain enzymes, particularly serine proteases, which play a crucial role in various biological processes.

Uses

Used in Pharmaceutical Industry:
Ethanesulfonic acid isopropyl ester is used as a serine protease inhibitor for the purpose of controlling blood glucose levels. By inhibiting the activity of serine proteases, this compound can help regulate the enzymes responsible for the increase in blood glucose, making it a potential candidate for the development of drugs to manage diabetes and other related conditions.

InChI:InChI=1/C5H12O3S/c1-4-9(6,7)8-5(2)3/h5H,4H2,1-3H3

Synthetic route

isopropyl alcohol (67-63-0) + Ethanesulfonyl chloride (594-44-5) → isopropyl ethanesulfonate (14245-62-6)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 3h;	75%
With triethylamine In dichloromethane for 0.333333h;	60%
With 2,6-dimethylpyridine; sulfuric acid for 2.5h; Ambient temperature;	48%
With triethylamine In dichloromethane at 20℃; Rate constant;

sodium isopropylate (683-60-3) + Ethanesulfonyl chloride (594-44-5) → isopropyl ethanesulfonate (14245-62-6)

isopropyl methanesulfonate (926-06-7) + methyl iodide (74-88-4) → isopropyl ethanesulfonate (14245-62-6)

Conditions	Yield
(i) nBuLi, hexane, THF, (ii) /BRN= 969135/; Multistep reaction;

isopropyl ethanesulfonate (14245-62-6) + diethyl chlorophosphate (814-49-3) → 1-(diethylphosphono)ethanesulfonic acid isopropyl ester (1311290-66-0)

Conditions	Yield
Stage #1: isopropyl ethanesulfonate With n-butyllithium In tetrahydrofuran at -78℃; for 0.333333h; Stage #2: diethyl chlorophosphate In tetrahydrofuran at -78℃; for 0.5h;	58%

isopropyl ethanesulfonate (14245-62-6) + methyl iodide (74-88-4) → 2-propyl 2-propanesulfonate ester (27907-12-6)

Conditions	Yield
(i) nBuLi, hexane, THF, (ii) /BRN= 969135/; Multistep reaction;

4-Nitrobenzylpyridin (1083-48-3) + isopropyl ethanesulfonate (14245-62-6) → Ethanesulfonate1-isopropyl-4-(4-nitro-benzyl)-pyridinium;

Conditions	Yield
With phosphate buffer; water In acetone at 37℃; Product distribution; pH 6.0;

Upstream product

• 67-63-0 isopropyl alcohol 
• 594-44-5 Ethanesulfonyl chloride 
• 926-06-7 isopropyl methanesulfonate 
• 74-88-4 methyl iodide 
• 683-60-3 sodium isopropylate 

Relevant articles and documents

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Process for preparation of oxyglutaric acid ester derivatives

A process for preparing an oxyglutaric acid ester derivative of the formula: STR1 in which each of R1 and R2 is C1-5 alkoxy, C1-7 aralkyloxy, C7-9 halogenated aralkyloxy or phenyl, R4 is a hydroxyl-protecting group, and R5 is C1-10 alkyl which may have a substituent, comprises the steps of reacting a methyl phosphonate derivative or methyl phosphine oxide derivative with an oxyglutaric acid mono-ester to give a reaction product which comprises an oxyglutaric acid derivative having a phosphorus-containing group and a pentenedioic acid mono-ester (by-product), removing the pendenedioic acid mono-ester from the reaction product to isolate the oxyglutaric acid derivative, and converting the isolated oxyglutaric acid derivative into the oxyglutaric acid ester derivative. A process for obtaining an optically active oxyglutaric acid ester derivative is also disclosed.

Studies on chemical carcinogens and mutagens. XXV. Chemoselectivity of alkyl sulfonates toward 4-(p-nitrobenzyl)pyridine (NBP) in phosphate buffer

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